Diethylene glycol
Encyclopedia : D : DI : DIE : Diethylene glycol
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| Chemical name | |
| Other names | diethylene glycol ethylene diglycol diglycol 2,2'-oxybisethanol 3-oxa-1,5-pentanediol dihydroxy diethyl ether |
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| Density | 3 |
| Melting point | °C> |
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| [Chemical infoboxDisclaimer and references] | |
Diethylene glycol (DEG) is a diol, an alcohol with two -OH groups, a dimer of ethylene glycol. Its molecular structure is HO-CH2-CH2-O-CH2-CH2-OH. It is a clear, hydroscopic, odorless liquid. It is miscible with water, alcohols, diethyl ether and acetone, but insoluble in benzene and carbon tetrachloride.
Triethylene glycol (TEG, or triglycol) and tetraethylene glycol are trimers and tetramers of ethylene glycol, with formulas HO-CH2-CH2-O-CH2-CH2-O-CH2-CH2-OH and HO-CH2-CH2-O-CH2-CH2-O-CH2-CH2-O-CH2-CH2-OH.
Uses
Like ethylene glycol, a mix of diethylene glycol and water is used as a coolant. It lowers the freezing point of the mixture, making it suitable for use in low temperature climates, but it also raises its boiling point, higher than ethylene glycol itself, making it more suitable for hot climates. It is also used in synthesis of morpholine and 1,4-dioxane, and as a solvent for nitrocellulose, resins, dyes, oils, and some other organic compounds. It is a humectant for tobacco, cork, printing ink, and glue. It can be also found in some hydraulic fluids and brake fluids.
Triethylene glycol, a colorless odourless viscous liquid, has lower toxicity than diethylene glycol and is used as vinyl plasticizer and in air conditioning systems as a dehumidifier. When aerosolized, it acts as a disinfectant. It can be also found in some hydraulic fluids and brake fluids. Its CAS number is [112-27-6][link] and its SMILES structure is OCCOCCOCCO.
Glycols are used as liquid desiccants for dehydration of natural gas.
Safety and toxicity
Diethylene glycol has been responsible for a number of mass poisonings. The most famous incident was the 1937 Elixir Sulfanilamide disaster in the USA, in which 107 people died after taking sulfanilamide dissolved in diethylene glycol. This was the impetus for the Federal Food, Drug, and Cosmetic Act of 1938. In recent years, deaths from medicines adulterated with diethylene glycol have been reported from South Africa, India, Nigeria, and Haiti.In 1985 a scandal broke when diethylene glycol appeared to be added as an adulterant by a number of vintners of Austrian white wines, in order to make them sweeter and upgrade the dry wines to sweet wines; production of sweet wines is expensive and addition of sugar is easy to detect. The amount added was not high enough to be immediately toxic (one would have to ingest about 28 bottles per day for two weeks); however, the adverse worldwide publicity caused very high export losses and led to adoption of severe wine laws in Austria.
Reference
- Merck Index, 12th Edition, 3168.
See also
- Ethylene glycol
- Polyethylene glycol
- [Diethylene Glycol]
- [Triethylene Glycol]
- [The Elixir Sulfanilamide Disaster]
External links
- For a full list of external links to MSDSs, spectroscopic data, commercial chemicals suppliers etc. for this compound, see [Chemical sources].
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